We are debating whether to go the week of Memorial day (last week of May) or the first week in October.
We went in October last year and it was great in terms of weather and crowds, but my son had to miss 3 days of school (okay, but not ideal).
We went in late may two years ago and it was super hot, but it was a no-parks trip, so we spent most of our time at the pool. This time we’ll likely visit MK once.
I’m leaning towards May because of a) school and b) less time to wait before our trip …however, ticket prices are higher in May, it can get pretty hot, and we’ll have limited resort choices (if we rent DVC).
As for crowds, I’m guessing late May is pretty bad? October wasn’t bad at all, but I hear that things are getting busier in the Fall.